((1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl)boronic acid | 550364-43-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: ((1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl)boronic acid
• 英文别名: (1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-enyl)buta-1,3-dienylboronic acid；[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)buta-1,3-dienyl]boronic acid
• CAS: 550364-43-7
• 化学式: C₁₄H₂₃BO₂
• 分子量: 234.146
• InChiKey: QQOJRUXQVXQTIK-ZDVGBALWSA-N

物化性质

• 沸点：
  377.6±25.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl)boronic acid 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate potassium phosphate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 11.17h， 生成 视黄醛
  参考文献：
  名称：

  [EN] AUTOMATED SYNTHESIS OF SMALL MOLECULES USING CHIRAL, NON-RACEMIC BORONATES
  [FR] SYNTHÈSE AUTOMATISÉE DE PETITES MOLÉCULES À L'AIDE DE BORONATES NON RACÉMIQUES, CHIRAUX

  摘要：

  公开号：

  WO2012149182A3
• 作为产物：
  描述：

  (E)-丁烯-3-炔基-2,6,6-三甲基-1-环己烯 在 正丁基锂 、 甲基镁三丁基锡烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 ((1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl)boronic acid
  参考文献：
  名称：

  Trienylboronic acid, a versatile coupling tool for retinoid synthesis; stereospecific synthesis of 13-aryl substituted (11Z)-retinal

  摘要：

  Trienylboronic acid 1a was prepared from iodotriene 3, which was coupled with (2Z,4Z)-3-aryl-5-iodo-2,4-pentadienol 9 by Suzuki coupling reaction to give geometrically pure 13-aryl substituted (11Z)-retinol 10. Oxidation of 10 gave 13-aryl substituted (11Z)-retinal 11. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00550-1

文献信息

• Simple, Efficient, and Modular Syntheses of Polyene Natural Products via Iterative Cross-Coupling
  作者：Suk Joong Lee、Kaitlyn C. Gray、James S. Paek、Martin D. Burke

  DOI：10.1021/ja078129x

  日期：2008.1.1

  versatile B-protected haloalkenylboronic acid building blocks for iterative cross-coupling. These reagents enable the total synthesis of polyene natural products with extraordinary levels of simplicity, efficiency, and modularity. Specifically, all-trans-retinal, β-parinaric acid, and one-half of the amphotericin B macrolide skeleton were prepared using only the Suzuki−Miyaura reaction in an iterative manner

  该通讯描述了空气稳定且高度通用的 B 保护卤代烯基硼酸构建块的发现，用于迭代交叉偶联。这些试剂使多烯天然产物的全合成具有非凡的简单性、效率和模块化水平。具体而言，仅使用 Suzuki-Miyaura 反应以迭代方式制备全反式视黄醛、β-肝素酸和二分之一的两性霉素 B 大环内酯骨架，以汇集简单且易于获取的构建块的集合。与其硼酸对应物相比，中间体多烯基硼酸酯非常稳定（对柱纯化和储存），这对其成功利用至关重要。此外，使用非常温和的碱水溶液可以干净地释放反应性硼酸。这些进步使人们能够使用 SM 反应制备最长的多烯。据我们所知，我们还报告了...
• Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes
  作者：Jared H. Delcamp、Paul E. Gormisky、M. Christina White

  DOI：10.1021/ja402891m

  日期：2013.6.12

  We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.
• [EN] AUTOMATED SYNTHESIS OF SMALL MOLECULES USING CHIRAL, NON-RACEMIC BORONATES<br/>[FR] SYNTHÈSE AUTOMATISÉE DE PETITES MOLÉCULES À L'AIDE DE BORONATES NON RACÉMIQUES, CHIRAUX
  申请人：UNIV ILLINOIS

  公开号：WO2012149182A3

  公开（公告）日：2013-01-24
• Trienylboronic acid, a versatile coupling tool for retinoid synthesis; stereospecific synthesis of 13-aryl substituted (11Z)-retinal
  作者：Jun'ichi Uenishi、Katsuaki Matsui、Akimori Wada

  DOI：10.1016/s0040-4039(03)00550-1

  日期：2003.4

  Trienylboronic acid 1a was prepared from iodotriene 3, which was coupled with (2Z,4Z)-3-aryl-5-iodo-2,4-pentadienol 9 by Suzuki coupling reaction to give geometrically pure 13-aryl substituted (11Z)-retinol 10. Oxidation of 10 gave 13-aryl substituted (11Z)-retinal 11. (C) 2003 Elsevier Science Ltd. All rights reserved.